US2016311952A1PendingUtilityA1

Crosslinked Polyolefins for Biomedical Applications and Method of Making Same

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Assignee: INNOLENE LLCPriority: Nov 8, 2007Filed: Jul 5, 2016Published: Oct 27, 2016
Est. expiryNov 8, 2027(~1.3 yrs left)· nominal 20-yr term from priority
Inventors:Yonghua ZhouLeonard Pinchuk
C08F 293/00A61L 27/16C08J 2353/00C08J 3/247C08F 210/10C08J 2323/22A61F 2002/1681A61F 2/1629C08F 212/32C08F 297/00A61F 2/1624C08F 210/14A61F 2/1613C08F 212/08G02B 1/043C08F 212/12C08F 212/06
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Claims

Abstract

The invention relates to a polymer composition that includes a branched alkene which is cationically polymerizable as well as a glass-forming comonomer and/or a vinyl comonomer containing benzocyclobutene as the pendant group. The structure of the polymer composition can take various forms: linear random copolymer, linear block copolymer, star random copolymer, star block copolymer, and other hyperbranched polymers. The copolymer composition can undergo crosslinking at elevated temperatures (preferably above 180° C.).

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . A method of preparing a copolymer comprising:
 cationic polymerizing a mixture including i) at least one branched alkene monomer, ii) at least one olefin monomer having a pendant benzocyclobutene (BCB) group, and iii) at least one initiator suitable for cationic polymerization of the mixture to form the copolymer;   wherein the copolymer formed by cationic polymerization of the mixture comprises a random distribution of a plurality of constitutional units that include constitutional units corresponding to the at least one branched alkene monomer of i) and constitutional units corresponding to the at least one olefin monomer having a pendant benzocyclobutene (BCB) group of ii);   wherein the branched alkene monomer of i) is an isoolefin selected from the group consisting of isobutylene, 2-methyl-1-butene, 2-methyl-1-pentene, 2-methyl-1-hexene, and combinations thereof; and   wherein the at least one initiator is selected from the group consisting of: a) organic ethers, b) organic esters, c) organic alcohols, d) organic halides, including tert-ester, tert-ether, tert-hydroxyl and tert-halogen containing compounds, e) alkyl cumyl ethers, cumyl halides, alkyl cumyl esters, cumyl hydroxyl compounds and hindered versions of the same, f) dicumyl chloride, g) 5-tert-butyl,1,3-dicumyl chloride, h) 5-tert-butyl-1,3-bis(1-methoxy-1-methylethyl)benzene, i) initiators having three or more initiation sites, j) tricumyl chloride (i.e., 1,3,5-tris(1-chloroy-1-methylethyl)benzene), k) Lewis acid initiators, l) metal halides, m) boron trichloride, n) titanium tetrachloride, o) alkyl aluminum halides, and p) combinations thereof.   
     
     
         2 . A method according to  claim 1 , wherein:
 the at least one initiator includes 5-tert-butyl, 1,3-dicumyl chloride.   
     
     
         3 . A method according to  claim 1 , wherein:
 the at least one initiator includes 5-tert-butyl-1,3-bis(1-methoxy-1-methylethyl)benzene.   
     
     
         4 . A method according to  claim 1 , wherein:
 the at least one initiator includes 1,3,5-tris(1-chloroy-1-methylethyl)benzene.   
     
     
         5 . A method according to  claim 1 , wherein:
 the at least one initiator includes 5-tert-butyl-1,3-bis(1-methoxy-1-methylethyl)benzene and 1,3,5-tris(1-chloroy-1-methylethyl)benzene.   
     
     
         6 . A method according to  claim 1 , wherein:
 the isoolefin is isobutylene.   
     
     
         7 . A method according to  claim 1 , wherein:
 the at least one olefin monomer having a pendant BCB group includes a monomer having the formula   
       
         
           
           
               
               
           
         
         wherein R is hydrogen or an alkyl group and n is 0. 
       
     
     
         8 . A method according to  claim 7 , wherein:
 the at least one olefin monomer having a pendant BCB group includes 4-vinylbenzocyclobutene or 2-(4-benzocyclobutenyl)-propene.   
     
     
         9 . A method according to  claim 1 , wherein:
 the at least one olefin monomer having a pendant BCB group includes a monomer having the formula   
       
         
           
           
               
               
           
         
         wherein R is alkyl group and n is an integer ranging from 0-3. 
       
     
     
         10 . A method according to  claim 9 , wherein:
 the at least one olefin monomer having a pendant BCB group includes 2-methyl-3-(4-benzocyclobutenyl)-propene.   
     
     
         11 . A method according to  claim 1 , wherein:
 the copolymer further includes a glass-forming monomer selected from the group consisting of styrene, indene, α-methylstyrene, p-tert-butylstyrene, p-chlorostyrene, norbornene, and combinations thereof.   
     
     
         12 . A method according to  claim 11 , wherein:
 the glass-forming monomer is styrene.   
     
     
         13 . A method according to  claim 1 , wherein:
 the at least one olefin monomer having a pendant BCB group is present in amount ranging from 0.01 to 60 mol % of the monomeric units of the thermoplastic polymer.   
     
     
         14 . A method according to  claim 1 , wherein:
 the cationic polymerizing involves living cationic polymerization.   
     
     
         15 . A method according to  claim 1 , wherein:
 the copolymer undergoes crosslinking when exposed to temperatures of at least 180° C.   
     
     
         16 . A method according to  claim 1 , wherein:
 the at least one branched alkene monomer of i) and the at least one olefin monomer having a pendant benzocyclobutene (BCB) group of ii) are added contemporaneously to the mixture during the cationic polymerizing of the mixture.   
     
     
         17 . A method of preparing a thermoset polymer comprising:
 processing a copolymer prepared according to  claim 1  to form a resultant thermoset polymer, wherein the processing includes heating the copolymer such that the copolymer undergoes crosslinking to form the resultant thermoset polymer.   
     
     
         18 . A method of preparing an implantable medical device comprising:
 processing a copolymer prepared according to  claim 1  to form at least part of the implantable medical device, wherein the processing includes heating the copolymer such that the copolymer undergoes crosslinking to form a resultant thermoset polymer that is part of the implantable medical device.   
     
     
         19 . A method according to  claim 18 , wherein:
 the implantable medical device comprises an intraocular lens.   
     
     
         20 . A thermoset polymer comprising:
 a random distribution of a plurality of constitutional units that include first and second constitutional units with at least one initiator;   wherein the first constitutional units are derived from at least one cationically polymerizable branched alkene monomer, wherein the branched alkene monomer is an isoolefin selected from the group consisting of isobutylene, 2-methyl-1-butene, 2-methyl-1-pentene, 2-methyl-1-hexene, and combinations thereof;   wherein the second constitutional units are derived from at least one cationically polymerizable olefin monomer having a pendant benzocyclobutene (BCB) group;   wherein the at least one initiator is selected from the group consisting of: a) organic ethers, b) organic esters, c) organic alcohols, d) organic halides, including tert-ester, tert-ether, tert-hydroxyl and tert-halogen containing compounds, e) alkyl cumyl ethers, cumyl halides, alkyl cumyl esters, cumyl hydroxyl compounds and hindered versions of the same, f) dicumyl chloride, g) 5-tert-butyl,1,3-dicumyl chloride, h) 5-tert-butyl-1,3-bis(1-methoxy-1-methylethyl)benzene, i) initiators having three or more initiation sites, j) tricumyl chloride (i.e., 1,3,5-tris(1-chloroy-1-methylethyl)benzene), k) Lewis acid initiators, l) metal halides, m) boron trichloride, n) titanium tetrachloride, o) alkyl aluminum halides, and p) combinations thereof; and   wherein the copolymer is crosslinked by application of heat.   
     
     
         21 . A thermoset polymer according to  claim 20 , wherein:
 the at least one initiator includes 5-tert-butyl, 1,3-dicumyl chloride.   
     
     
         22 . A thermoset polymer according to  claim 20 , wherein:
 the at least one initiator includes 5-tert-butyl-1,3-bis(1-methoxy-1-methylethyl)benzene.   
     
     
         23 . A thermoset polymer according to  claim 20 , wherein:
 the at least one initiator includes 1,3,5-tris(1-chloroy-1-methylethyl)benzene.   
     
     
         24 . A thermoset polymer according to  claim 20 , wherein:
 the at least one initiator includes 5-tert-butyl-1,3-bis(1-methoxy-1-methylethyl)benzene and 1,3,5-tris(1-chloroy-1-methylethyl)benzene.   
     
     
         25 . A thermoset polymer according to  claim 20 , wherein:
 the isoolefin is isobutylene.   
     
     
         26 . A thermoset polymer according to  claim 20 , wherein:
 the at least one olefin monomer having a pendant BCB group includes a monomer having the formula   
       
         
           
           
               
               
           
         
         wherein R is hydrogen or an alkyl group and n is 0. 
       
     
     
         27 . A thermoset polymer according to  claim 26 , wherein:
 the at least one olefin monomer having a pendant BCB group includes 4-vinylbenzocyclobutene or 2-(4-benzocyclobutenyl)-propene.   
     
     
         28 . A thermoset polymer according to  claim 20 , wherein:
 the at least one olefin monomer having a pendant BCB group includes a monomer having the formula   
       
         
           
           
               
               
           
         
         wherein R is alkyl group and n is an integer ranging from 0-3. 
       
     
     
         29 . A thermoset polymer according to  claim 28 , wherein:
 the at least one olefin monomer having a pendant BCB group includes 2-methyl-3-(4-benzocyclobutenyl)-propene.   
     
     
         30 . A thermoset polymer according to  claim 20 , further comprising:
 a glass-forming component selected from the group consisting of styrene, indene, α-methylstyrene, p-tert-butylstyrene, p-chlorostyrene, norbornene, and combinations thereof.   
     
     
         31 . A thermoset polymer according to  claim 20 , which is crosslinked by application of heat at a temperature of at least 180° C.

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